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Synthesis of plodia interpunctella sex pheromone 9Z, 12E-tetradecadiene-1-acetate

A technology of alcohol acetate and pheromone, which is applied in the field of synthesis of sex pheromone 9Z, 12E-tetradecadien-1-ol acetate of Indian meal moth, can solve problems such as limitation of control methods, and achieve reduction The effect of production cost, mild reaction conditions and shortened production cycle

Inactive Publication Date: 2014-03-12
昆明博鸿科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] With the increasing concern about environmental issues and human health, traditional methods of controlling Indian meal moth with chemical insecticides are becoming more and more limited in storage facilities

Method used

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  • Synthesis of plodia interpunctella sex pheromone 9Z, 12E-tetradecadiene-1-acetate
  • Synthesis of plodia interpunctella sex pheromone 9Z, 12E-tetradecadiene-1-acetate

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1 9-hydroxy nonanol acetate ( 3 ) preparation: Dissolve 1,9-nonanediol (16 g, 0.1 mol) in 450 ml of petroleum ether, add a catalytic amount of 98% concentrated sulfuric acid, slowly add glacial acetic acid (6 g, 0.1 mol) in 50 ml of petroleum Ether solution, continue to reflux at 60-90°C for 18 hours after dripping, stop the reaction, add saturated sodium carbonate to neutralize to pH=7-8, separate the petroleum ether layer, extract the water layer with petroleum ether for 3 times, combine the organic layer, dried over anhydrous sodium sulfate and distilled off the solvent under reduced pressure to obtain a crude product, which was purified by column chromatography (petroleum ether and ethyl acetate as the eluent) to obtain 9-hydroxynonanol acetate ( 3 ) 16.3 g, yield 81%.

Embodiment 2

[0019] Embodiment 2 9-Oxononanol acetate ( 4 ) preparation: 9-hydroxynonanol acetate ( 3 ) (16.2 g, 80 mmol) was dissolved in 400 ml of dry dichloromethane, cooling in an ice bath and adding pyridinium chlorochromate (25.86 g, 120 mmol) in batches under stirring, stirring at room temperature for 3 hours, adding an appropriate amount of water, separated dichloromethane, and extracted 2 times with dichloromethane, combined the organic layers, dried over anhydrous sodium sulfate and evaporated the solvent to obtain a crude product, which was purified by column chromatography (eluent was petroleum ether and ethyl acetate ) was purified to obtain 9-oxononanol acetate ( 4 ) 12.3 g, yield 77%, the crude product can also be directly used in the next reaction.

Embodiment 3

[0020] Example 3 5-bromo-3E-pentene ( 6 ) preparation: Dissolve trans-3-penten-1-ol (0.15 mol, 12.9 g) in 150 ml of dry dichloromethane, add phosphorus tribromide (55 mmol, 14.9 g) dropwise, continue to After stirring in an ice bath for 3 hours, add saturated sodium carbonate to neutralize to pH = 7-8, separate the organic layer, extract the water layer once with dichloromethane, combine the organic layers, dry over anhydrous sodium sulfate and evaporate under reduced pressure. Obtain crude product after solvent removal, obtain 5-bromo-3E-pentene ( 6 ) 17.0 g, yield 76%.

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Abstract

The invention discloses a synthesis method of plodia interpunctella sex pheromone 9Z, 12E-tetradecadiene-1-acetate. According to the synthesis method, 1, 9-nonanediol and 3E-pentene-1-ol are taken as initial raw materials. The synthesis method comprises following steps: 9-hydroxy nonanol acetate is obtained via single esterification of 1, 9-nonanediol; a key intermediate 9-oxo nonanol acetate is obtained via oxidation of pyridinium chlorochromate; 5-bromo-3E-pentene is obtained via bromination of 3E-pentene-1-ol; 3E-pentenyl benzyltriphenylphosphonium bromide is obtained via reaction of 5-bromo-3E-pentene with triphenylphosphine; and 3E-pentenyl benzyltriphenylphosphonium bromide is processed with an organic acid, and then is subjected to Wittig reaction with 9-oxo nonanol acetate so as to obtain (9Z, 12E)-tetradecadiene-1-acetate. Advantages of the synthesis method are that: raw materials are cheap and easily available; synthesis route is simple; reaction conditions are mild; operation is convenient and safe; yield is high; and cost is low.

Description

technical field [0001] The invention relates to a method for synthesizing the sex pheromone 9Z, 12E-tetradecadien-1-ol acetate of Indian meal moth. Background technique [0002] Indian meal moth (Plodia interpunctella Hübner) belongs to Lepidoptera Lepidopteridae. It is native to Europe and has been widely distributed in all countries in the world. It is one of the most harmful storage pests in the world. It has not been found in my country except Tibet. All provinces and autonomous regions are distributed. The Indian meal moth has a wide range of feeding habits and harms almost every kind of plant storage. It uses larvae to damage various grains and processed products, oil plants such as beans and flax, nuts such as peanuts, dried fruits such as raisins, dried vegetables, milk powder, Chinese medicinal materials and tobacco leaves, etc. Among them, cereals, soybeans, red dates and grain flour are the most severely damaged. [0003] As people pay more and more attention to ...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293
CPCC07C67/293C07C17/16C07C67/08C07C67/29C07F9/5428C07C69/145C07C69/12C07C69/16C07C21/14
Inventor 陶云海黄飞杨婉秋
Owner 昆明博鸿科技有限公司
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